Nonchiral ionic liquids have been used as solvents in the past. Chiral liquids that are racemic have been used as solvents as well. See Yasuhiro Ishida et al., “Design and synthesis of a novel imidazolium-based ionic liquid with planar chirality,” Chem. Commun. 2240-41 (2002) (a copyright of the Royal Society of Chemistry). Solvents of enantiomerically enhanced chiral cations have also been described. See Wasserscheid et al., “Synthesis and properties of ionic liquids derived from the ‘chiral pool’,” Chem. Commun. 200-01 (2002) and Weiliang Bao et al., “Synthesis of Chiral Ionic Liquids from Natural Amino Acids,” 68 J. Org. Chem. 591 (2003). These were not described as vehicles for conducting subsequent reactions.
Earle et al. disclosed reactions of dienes and dienophiles in various solvents including [bmim] [lactate], an ionic liquid with a chiral anion of unreported configuration or purity. The result was not asymmetric. See Martyn J. Earle et al., “Diels-Alder reactions in ionic liquids,” Green Chem. 23-25 (1999). Chiral nonionic materials have also been used as the stationary phases in gas chromatography. (See U.S. Pat. Nos. 4,948,395 and 5,064,944.)